title: One-pot synthesis of 1,2-dihydropyridines: expanding the diverse reactivity of propargyl vinyl ethers.
abstract: The catalyzed synthesis of 1,2-dihydropyridines starting from easily accessible propargyl vinyl ethers was realized. The reaction sequence involving a transition metal-catalyzed propargyl-Claisen rearrangement, a condensation step, and a Brønsted acid-catalyzed heterocyclization furnishes the highly substituted heterocycles in moderate to excellent yields. Additionally, a practical one-pot protocol toward 1,2-dihydropyridines and 2H-pyrans starting from propargylic alcohols was developed.
authors.affiliation: Department Chemie and Catalysis Research Center, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany.
authors.forename: Tobias
authors.initials: T
authors.lastname: Harschneck
authors.forename: Stefan F
authors.initials: SF
authors.lastname: Kirsch
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D004987:Ethers; D011725:Pyridines; D014753:Vinyl Compounds; C531209:propargyl ether